Polyisobuteneamine (PIBA) is a

polymer A polymer () is a chemical substance, substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeat unit, repeating subunits derived from one or more species of monomers. Due to their br ...

derived from the reaction of

polyisobutylene Polyisobutene (polyisobutylene) is a class of organic polymers prepared by polymerization of isobutene. The polymers often have the formula Me3C H2CMe2sub>nH (Me = CH3). They are typically colorless gummy solids. Cationic polymerization, initia ...

(PIB) with

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

primary amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

s. This polymeric compound is known for its excellent adhesive and dispersant properties and is commonly used as an additive in

lubricant A lubricant (sometimes shortened to lube) is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces, ...

s, fuel, and other industrial applications.

History of discovery

The history of polyisobuteneamine dates back to the early development and study of polyisobutylene. The first synthesis of polyisobutylene was reported in 1931 by the German chemists

Hermann Staudinger Hermann Staudinger (; 23 March 1881 – 8 September 1965) was a German organic chemist who demonstrated the existence of macromolecules, which he characterized as polymers. For this work he received the 1953 Nobel Prize in Chemistry. He is also ...

and Leonidas Zechmeister, who obtained the polymer through the cationic polymerization of

isobutylene Isobutylene (or 2-methylpropene) is a hydrocarbon with the chemical formula . It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value. Product ...

. The discovery of polyisobuteneamine followed as researchers began to explore the potential applications of polyisobutylene and its derivatives.

Synthesis

Polyisobuteneamine is synthesized through the reaction of polyisobutylene with ammonia or primary amines in the presence of a catalyst. The reaction takes place at elevated temperatures and pressures. The molecular weight of the resulting polymer can be controlled by adjusting the reaction conditions and the choice of catalyst. Polyisobutylene (PIB): (CH₂=C(CH₃)₂)_n Ammonia (NH₃) or Primary amine (RNH₂) Polyisobuteneamine (PIBA): (CH₂-C(CH₃)₂)N(H)-sub>m In the chemical formulas above, n represents the degree of polymerization of PIB, R represents a hydrogen atom (in the case of ammonia) or an alkyl group (in the case of primary amines), and m is the degree of substitution of the amine group on the polyisobutylene backbone.

Properties

Polyisobuteneamine is a viscous liquid with a yellow to amber color. It has excellent adhesion and

dispersant A dispersant or a dispersing agent is a substance, typically a surfactant, that is added to a suspension of solid or liquid particles in a liquid (such as a colloid or emulsion) to improve the separation of the particles and to prevent their sett ...

properties, which are attributed to its polar amine groups and nonpolar polyisobutylene backbone. The unique combination of polar and nonpolar groups allows PIBA to interact with a wide range of materials, making it a versatile additive.Mart, L. (ed.). (2013). Handbook of Plasticizers, 2nd Edition. Elsevier.

Applications

Polyisobuteneamine is commonly used as an additive in lubricants, fuel, and other industrial applications. Its adhesive and dispersant properties make it particularly useful in enhancing the performance of

engine oil Motor oil, engine oil, or engine lubricant is any one of various substances used for the lubrication of internal combustion engines. They typically consist of base oils enhanced with various additives, particularly antiwear additives, deter ...

gear oil Gear oil is a lubricant made specifically for transmissions, transfer cases, and differentials in automobiles, trucks, and other machinery. It has high viscosity and usually contains organosulfur compounds. Some modern automatic transaxles ...

s, and

hydraulic fluid A hydraulic fluid or hydraulic liquid is the medium by which power is transferred in hydraulic machinery. Common hydraulic fluids are based on mineral oil or water. Examples of equipment that might use hydraulic fluids are excavators and backho ...

s. PIBA is also used in

fuel additive Gasoline additives may increase gasoline's octane rating, thus allowing the use of higher compression ratios for greater efficiency and power, or act as corrosion inhibitors or lubricants. Other additives include metal deactivators, oxygenates an ...

s to improve the combustion process and reduce deposits in the engine. Other applications include the use of PIBA as a

corrosion inhibitor A corrosion inhibitor or anti-corrosive is a chemical compound added to a liquid or gas to decrease the corrosion rate of a metal that comes into contact with the fluid. The effectiveness of a corrosion inhibitor depends on fluid composition and ...

, an

emulsifier An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Althou ...

, and a

demulsifier Demulsifiers, or emulsion breakers, are a class of specialty chemicals used to separate emulsions, for example, water in oil. They are commonly used in the processing of crude oil, which is typically produced along with significant quantities of sa ...

in various industrial processes.

References

* Staudinger, H., & Zechmeister, L. (1931). Über Polymerisation. Berichte der deutschen chemischen Gesellschaft (A and B Series), 64(9), 2157-2160. * Legge, N. R., Holden, G., & Schroeder, H. (eds.). (2005). Thermoplastic Elastomers: A Comprehensive Review. iSmithers Rapra Publishing. * Mart, L. (ed.). (2013). Handbook of Plasticizers, 2nd Edition. Elsevier.

Notes

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External links

JP4197298B2 - Polyisobuteneamine - Google Patents

Synthesis of 1-polyisobuteneamine-(2-¹⁴C)

Effect of Multifunctional Fuel Additives on Octane Number Requirement of Internal Combustion Engines 932813
Polymers Plasticizers